Tetrahedron p. 5815 - 5824 (1989)
Update date:2022-07-29
Topics:
Aurich, Hans Guenther
Moebus, Klaus-Dieter
Upon oxidation of hydroxylamines 1a-c only nitrones 2a-c could be isolated although the nitroxides 3a-c were detected by ESR.Oxidation of 1f yields compound 5, the CC-dimer of 4.Whereas oxidation of 1d affords only 7d which arises from 3d by CC-dimerization and elimination of propylsulfinic acid, from vinyl nitroxide 3e products 7e, 8 and 9 are formed by CC-dimerization and subsequent reaction steps, as well as 11 which is formed via the intermediate OC-dimer 10.The reaction steps leading to the different products are discussed.The reactivity of vinyl nitroxides can be attributed to their tendency to undergo bond formation at the β-C-atom.Thus, in principle they can form CC-bonded dimers or OC-bonded dimers.For N-tert-butyl substituted vinyl nitroxides CC-dimerization was found to be preferred reaction pathway at room temperature.It has been assumed that OC-dimers can be formed in a reversible reaction.However, if there is no possibility to form a more stable product in a subsequent reaction step, OC-dimerization should be only an unproductive reaction pathway.To verify this assumption we have now studied the dimerization of the corresponding hydroxylamines 1.
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